Sarah Louise Marr says...
Overall, a fantastic, well managed holiday. Highly recommended.
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In the heart of the Mediterranean lies Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas. We explore the very best of this captivating region from our start point in Alberobello, known for its UNESCO-listed Trulli houses, to the end point in Lecce, known as the 'Florence of the South'.
The daily routes take you through the Murghe plateau, the Salento plain or along the coast. Discover a landscape of ancient olive groves, long fields of grain and vineyards. The architecture of the region takes you from the conical Trulli houses in Alberobello, the white city of Ostuni, past traditional masserie, coastal watchtowers and splendid Baroque towns. The region is filled with spectacular views; beautiful coastline and mouth-watering cuisine.
This holiday is offered with a choice of mainly 3 Star, or mainly 4 Star accommodation. The 3 Star accommodation is listed on the hotels page.
95% of the cycling is on asphalt roads, with 5% on strada bianca. The routes generally keep to quieter, secondary roads although you should expect more traffic in the towns.
Make your way to Alberobello, famous for its Trulli houses.
Cycle through the lush Valle d'Itria, passing more white-tipped trulli houses on the way. Boasting beautiful coastal views, the route takes you through the famous wine town of Locorotondo, regarded as one of Italy's most stunning villages. After sampling some of the local sparkling white wine, continue to the white city of Ostuni - so called for the dazzling effect of its whitewashed houses.
Breakfast included
Cycle through the colourful Salentinian countryside, characterized by olive groves and red soil towards the medieval towns of Oria and Manduria with their authentic historic centres.
Breakfast and evening meal included
Head to Torre Colimena on the Ionian Sea, then follow the coast alongside a series of beaches and the old coastal towers of Salento. Reach Gallipoli, known as the 'Ionian Pearl' with its Old Town situated on a rocky island. Take time to wander the narrow lanes of the historic centre to discover its baroque cathedral, elegant palazzi and enticing restaurants.
Breakfast included
Cycle towards the most southerly point of Salento at Santa Maria di Leuca, where the crystal waters of the Ionian and Adriatic Sea meet. This village is home to one of the most important lighthouses in Italy, as well as numerous villas built at the turn of the century.
Breakfast included
Pedal along the south coast of the Adriatic Sea, stopping off at the famous Grotta Zinzulusa and the thermal baths of Santa Cesarea Terme. Your final destination is Otranto, the most eastern point of Italy with a stunning cathedral and Aragonese castle.
Breakfast included
Follow the shoreline through olive groves to the Baroque metropolis of Lecce. Known as the 'Florence of the South', Lecce is home to over 30 churches, an amphitheatre and a Roman theatre dating back to Emperor Augustus.
Breakfast included
During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.
To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
A unique and authentic experience staying in a trulli, a traditional 15th century Apulian stone building with conical roof.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
Situated a stone's throw from Ostuni's Old Town, the Relais Sant'Eligio dates back to the first half of the 1500s when Queen Bona Sforza d'Aragona imposed all coastal cities from Naples to Otranto to have a resting station. The Resting Station of Camposada - as it was then - has welcomed many couriers and royal officials from yesteryear, whilst today, each of the 22 elegant and individually decorated rooms offer every comfort for the 21st century guest.
Find out more on the hotel website.
Masseria Strazzati is an old farm estate and is set within 100 hectares of olive groves. Your evening meal is taken at the Masseria Bosco where the pool can also be used.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Located in the centre of Gallipoli and only a short walk from Corso Roma, Hotel Joli Park is modern and comfortable.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
Hotel Terminal is nestled among the eclectic villas, on the central nineteenth-century seafront dedicated to Cristoforo Colombo, the heart of the town, with a beautiful view on Punta Ristola and Punta Melis.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Located in the centre of Otranto, Hotel Albania owes its name to the majestic Albanian mountains which on a clear day offers guests breathtaking views and are visible from the hotel terrace.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
NEARBY:
Situated just outside of the historic town of Lecce, Hotel Eos is a modern hotel with modern facilities.If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.
Find out more on the hotel website.
Read customer reviews on Tripadvisor.
The Hotel Excelsior has large and bright rooms. There is also a bar and restaurant offering Mediterranean dishes.Transfers can be arranged at a supplement from Bari Airport at 14:20.
Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.
Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.
Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.
Overall, a fantastic, well managed holiday. Highly recommended.
I was extremely pleased with this holiday. I travelled early in the season (pre-Easter). There were good traffic-free sections, but in fact all the roads, even the main ones, were unbelievably quiet. You do have to understand that at this time practically everything is closed, sometimes entire small villages. On the other hand, it was even possible to cycle round the narrow medieval streets, which I imagine is not easy in the season. The routes chosen were ideal, scenic, quiet; I could not fault anything. While there are some beautiful cycle lanes, some of the road surfaces. especially in the country, are challenging, and there are good potholes. Be prepared for distressing levels of fly-tipping, even in some very rural areas.
Really well organised. Felt confident with all arrangements. Slight hiccough at the end when our itinerary said depart hotel for Bari at 1000 when it should have been 0900 but all ended well.
This trip was really fun and well organised. Would recommend
A fantastic holiday in a beautiful part of Italy. The locations each night were really varied from amazing farmhouse in the country to modern hotel overlooking the harbour.
Cycling varied from coast road to cycling through olive groves. Would definitely recommend.
We had a great holiday in Puglia. The countryside was lovely (except for the appalling litter problem which seems to blight southern Italy and Sicily), the towns were stunning and the length of cycling days just about perfect. The hotels were generally good, and the Masseria Bosco was outstanding. Swimming in warm seas on both sides of the region was very special, as were the gelati! The navigation app was brilliant - you really can't get lost (though you do have to be a bit careful in busy cities) and Headwater's communication was excellent.
We really enjoyed the route and accommodation, and felt we had seen so much of Puglia. The route is difficult to get to and from, but fortunately we have some friends who live in Puglia, so they picked us up from Brindisi airport, we stayed with them for a few days and then they drove us to Alberobello. I discovered, whilst we were there, we could have got back from Lecce to Brindisi by rail to meet the Sunday flight. Instead we had to rely on staying with our friends again for a few nights). This would have been very useful information to have upfront when planning a trip, and this is where Headwater are weak. You should be giving more information on how to get to places, from different uk airports, rather than just via the London airports. I think you’d get more customers (as we were surprised that we were the only two on this trip).
Very positive. The Puglia itinerary was excellent. The scenery was very varied: inland (vineyards, olive groves), beaches on the coast and cliffs on the coast. We visited some lovely towns / villages in Puglia and had the time to see them each day. Most of the roads were not too busy. The navigation app was superb at directing us.
Cycling holiday with Headwater was excellent and I would recommend this trip. We enjoyed the change of scenery from the inland routes of the first two days to the beautiful coastal routes of days 3, 4 and 5 - we spent two afternoons on the beaches which were outstanding. The trip have everything you need. The hotel in Gallipoli was only average but the remainder were very good. The family run hotel in Avetrana with a swimming pool was very special - staff amazing. We also loved the Hotel in Otranto where the staff were again great, the room was lovely and breakfast amazing with lots of choice. Overall the cycling was pleasant, not too challenging and a great way to see Italy. We will look to do similar holidays with Headwater and have recommended this to friends.
This tour around Puglia offers a varied insight into the region from the Trulli houses to resort hotels. Food and wine are consistently excellent and the hotel accommodation overall exceeded our expectations. The cycling, for the most part, is enjoyable. I would caveat that by saying some of the coastal roads are busy, even at the end of May/beginning of June and despite assurances from Antonio at the start of the tour that Italians treated cyclists with a degree of courtesy we found this to be generally not the case.
The cycling was fun and the app was generally easy to use though you should take an external battery pack. My phone was 3 years old and you need to set the screen to be quite bright so it uses up power quite quickly. The hotels that we used were all 3* but were comfortable. All hotels provided excellent breakfasts. We went in early May which is described as part of the holiday season but we found most places still closed so stopping off along the way wasn't as easy as we expected. One thing that we were really surprised by was the cost of transfers to and from the airport that Headwater wished to charge. Something like 240 from Bari to Arborobella (we caught a bus for 8 euros, and over 400 from Lecce back to Bari ( we caught the train for 24 euros). We hadn't been cycling for some years before booking this holiday but we practised for 5 weeks before going and we were fine.
Excellent. Superb trip, well organised.
Itinerary fine. Unfortunately weather not great do not a lot to do when cycling finished
Super. Cycling tour. Everything we needed was provided by friendly and efficient service. Highly recommended.
A great active holiday where you travel through different landscapes to arrive in interesting towns with lovely hotels.
Great route. Varying quality of hotels. Poor bikes. Expensive for what we got.
A very enjoyable holiday, staying at interesting places in good accommodation. We would certainly book with Headwater again for a cycling holiday
It was lovely to arrive at the end of a ride in the little towns of Puglia, all different and charming. Some of the cycling was really spectacular, particularly along the coast. I was pleased to have an e-bike as the temperature was way over 30 degrees everyday at the end of May. As someone not very tech-savvy, I needed help with the navigation app. Remember to download last-minute adjustments just before you go!
A great itinerary, a lot of variation in level of challenge.
This cycling route through Puglia is a stunningly beautiful one - particularly in late May when the poppies and other wild flowers were in full bloom; the weather warm but not scorching and not too busy with other tourists. This was the first Headwater cycling trip I have done without 'stay put' days, and the overall mileage each day (at leisurely pace) did mean there was little spare time for sightseeing. However, it was absolutely worth the effort to visit each of the locations - they were wonderfully varied and I wouldn't have wanted to miss out on any of them!
One of the days involves taking a train - it's worth noting that not all the trains allow bikes, and we were lucky to have had help lifting up the bikes into the hanging racks on the train - a tricky manouevre for the vertically challenged!
Fantastic way to see the glorious countryside, towns, cities and natural beauty of Puglia. Well organised, good bikes, good accommodation and we think the best way to immerse yourself in a location. As firstimers with Headwater would highly recommend to anyone.
Excellent. the App was easy to use for middle aged people who usually ask their children to work this kind of thing out. The Headwater emails were well timed and informative and when you passed us on to Gulia cycle tours, they were equally as efficient. The route was fantastic, the hotels just ideal for this holiday. The people we met from Puglia Tours delightful. We had 2 potentially big problems - A) one of our parties' bags didn't arrive from England on our flight. So we logged a missing bag form at Barri airport but it was difficult with language barrier and not knowing where we would be if and when the bag might catch up with us. Headwater were amazing and the bag caught us up 2 days later. And the driver from Puglio Tours took us from Barri airport to a hypermarket ( thank god open on a Sunday pm) to buy essentials. We also had a problem with a bike and again - fantastic backup and all sorted. Best holiday & when probs occurred the finest back up
An exceptional route - everything had been thought of. The first day is a long distance so it might be off putting for those who don’t cycle long distances regularly. The food everywhere is of a fantastically high standard. We recommend Le Bubbole in Matera, La Cantina in Alberobello and The Dish in Ostuni. Booking in advance recommended.
Our holiday was a celebration for our 30th wedding anniversary. In order to be consistent with the previous thirty years of marriage I left the planning until the last minute. I contacted Headwaters barely two weeks before the half term started yet they were able , as ever, to provide a first class service which totally met what we were looking for. From the moment we landed, where we met Mimmo our agent, until our departure from our gorgeous Lecce hotel on the final morning, we encountered nothing but an amazing service wherever we visited or stayed. We loved all of the accommodation as well as the stunning routes. Puglia is indeed an astonishingly beautiful region in Italy, as evidenced by the breath taking coastal routes to Gallipoli and Otranto. Likewise the climb to the hilltop town of Ostuni, as well the town itself, was simply stunning. I am running out of synonyms for brilliant but that is the adjective that I want to use to describe the everything about the trip. Thank you.
It was a well thought-out itinerary which took in the high-lights of Puglia - rural rides to beautiful hill-top towns and coastal rides with lovely views over the Mediterranean.
Excellent holiday with good hotels, great scenery and realistic riding days for the described activity level. The bikes were excellent and comfortable.
This was our first cycling holiday (we are in our seventies) We had the most enjoyable time, meeting up with fellow cyclist from other countries on route
The towns we stayed in and the hotel were all very good. The cycling was almost all on quiet roads. We would certainly like to book another trip. Mary and Tim
You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.
This 7 night self-guided cycling holiday includes:
Hotel-to-hotel accommodation in a mix of , and hotels
All breakfasts and 1 evening meal
Bike fitting and briefing at the start of your holiday
Headwater navigation app for your smartphone
Bike hire
Luggage transfers between hotels
How to book:
To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.
To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.
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22nd Apr 2024 | US$2345 | US$306 | Tour only: US$2345 Single supp: US$306 |
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2nd May 2024 | US$2480 | US$426 | Tour only: US$2480 Single supp: US$426 |
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12th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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15th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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17th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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19th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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22nd May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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24th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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26th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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29th May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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31st May 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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Departing | Tour only | Prices | Single supplement | |
---|---|---|---|---|
2nd Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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5th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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7th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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9th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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12th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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14th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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16th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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19th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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21st Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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23rd Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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26th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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28th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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30th Jun 2025 | US$2645 | US$426 | Tour only: US$2645 Single supp: US$426 |
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Departing | Tour only | Prices | Single supplement | |
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3rd Jul 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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5th Jul 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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7th Jul 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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10th Jul 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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12th Jul 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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14th Jul 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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Departing | Tour only | Prices | Single supplement | |
---|---|---|---|---|
25th Aug 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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28th Aug 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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30th Aug 2025 | US$2825 | US$426 | Tour only: US$2825 Single supp: US$426 |
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Departing | Tour only | Prices | Single supplement | |
---|---|---|---|---|
1st Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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4th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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6th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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8th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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11th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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13th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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15th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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18th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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20th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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22nd Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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25th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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27th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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29th Sep 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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Departing | Tour only | Prices | Single supplement | |
---|---|---|---|---|
2nd Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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4th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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6th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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9th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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11th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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13th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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16th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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18th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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20th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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23rd Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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25th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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27th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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30th Oct 2025 | US$2690 | US$426 | Tour only: US$2690 Single supp: US$426 |
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Departing | Tour only | Prices | Single supplement | |
---|---|---|---|---|
1st Nov 2025 | US$2255 | US$426 | Tour only: US$2255 Single supp: US$426 |
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3rd Nov 2025 | US$2255 | US$426 | Tour only: US$2255 Single supp: US$426 |
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6th Nov 2025 | US$2255 | US$426 | Tour only: US$2255 Single supp: US$426 |
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8th Nov 2025 | US$2255 | US$426 | Tour only: US$2255 Single supp: US$426 |
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10th Nov 2025 | US$2255 | US$426 | Tour only: US$2255 Single supp: US$426 |
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Check availability |
The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.
Solo travellers
Please call for details and prices
Children
This holiday is unsuitable for children.
Holiday type
Self-guided cycling Managed by Headwater rep.
Departures
Saturdays, Mondays and Thursdays from 22nd Apr 2024 to 10th Nov 2025, for 7 nights. All dates are subject to availability, please contact us to check.
Meals
All breakfasts and 1 evening meal
Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £256 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.
Other details
This holiday is also available with mainly 4 Star accommodation.
This holiday does not include any flights or rail.
To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.
If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.
To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.